• Title, Summary, Keyword: flavonoids

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Pharmacological Activities of Flavonoids (I) -Relationships of Chemical Structure of Flavonoids and their Inhibitory Activity of Hypersensitivities- (Flavonoids의 약리작용(I) -Flavonoids 구조와 과민반응 억제작용과의 상관성-)

  • Kim, Chang-Johng;Chung, Jin-Mo
    • YAKHAK HOEJI
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    • v.34 no.5
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    • pp.348-364
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    • 1990
  • The activities of twenty-one flavonoids and their related compounds on the hypersensitivity reaction against various antigens were studied in vitro and in vivo. 1. Generally flavonoids inhibited significantly the homologous passive cutaneous anaphylaxis (PCA) induced by reaginic antibody as compared as anaphylaxis by compound 48/80-induced mast cell degranulation, and so more strongly active in the IgE-mediated anaphylaxis than non-IgE-mediated anaphylaxis. 2. Flavonids inhibited remarkably Arths reaction, hemolysin titer, delayed hypersensitivity, haemagglutinin titer, rosette forming cells and plague forming cells against sheep red blood cells, and so it exhibited that flavonoids inhibited type 2, 3 and 4 hypersensitivity. 3. Quercetin, kaempferol, hesperetin, disodium cromoglycate, malvin and baicalein were active dose-dependently in the all types of hypersensitivity. Fisetin, daidzein, morin, narigin, flavone, catechin, rutin, hesperidin, neophsperidin, apigenin and chrysin were significantly active in the various types of hypersensitivity, but apigenin, rutin and catechin were less active in the delayed hypersensitivity. Taxifolin was significantly active in PCA and histamine-induced anaphylaxis except other types of hypersensitivity. Rotenone and cyanin also inhibited all types of hypersensitivity, but they are toxic. 4. Based on these results from hypersensitivity, the following flavonoid structure-activity relationships became apparent. 1) Flavonoids with $C_{2-3}$ double bond in C-ring were more active than that of $C_{2-3}$ saturation. 2) Flavonoids with $C_4$ ketone group in C-ring were more active than abscence of them except catechin and malvin. 3) Flavonoids with benzene ring at positions 2 or 3 in C-ring exhibited same activities. 4) Flavonoids with opening of the C-ring does not abolish their activities. 5) The glycosylated flavonoids in position 3 or 7 was less active than their aglycone. 6) Flavonoids with the more hydroxy group in A and B-ring were more active. 7) Flavonoids with or without $C_3-OH$ did not change their activities.

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Antioxidant Activity of Flavonoids in Plant Origin Food (식물성 식품에 존재하는 Flavonoids의 항산화 활성)

  • 김건희;최미희
    • Korean Journal of Food Preservation
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    • v.6 no.1
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    • pp.121-135
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    • 1999
  • Effective synthetic antioxidants such as butylated hydroxyanisole(BHA) and butylated hydroxytoluene(BHT) have been widely used in the food industry, but they are suspected to be toxic and carcinogenic effects. Therefore, the development of safely available natural antioxidants such as ascorbic acid, ${\alpha}$-tocopherol, ${\beta}$-carotene, flavonoids and selenium is essential. In particular, flavonoids, 2-phenyl-benzo-${\alpha}$-pyrones, are polyphenolic compounds that occur ubiquitously in food of plant origin. flavonoids occur in foods generally as O-glycosides with sugars bound usually at the C\ulcorner position. And variations in their heterocyclic ring gibes rise to flavones, flavonols, flavanones, flavanols, catechins, anthocyanidins, chalcone and isoflavones. Vegetables, fruits, and beverages are the main dietary sources of the flavonols, primarily as quercetin, kaempferol, and myricetin and the corresponding flavones, apigenin and luteolin. These flavonoids have biological activity such as antioxidant, anti-inflammatory, antithrombotic, antimutagenic, anticarcimogenic antiallergic and antimicrobial activity effects in vitro and in vivo. Flavonoids posses strong antioxidant activities acting as oxygen radicals scavenger, metal chelators and enzyme inhibitor. The antioxidant activity of flavonoids is determined by their molecular structure and more specially, by the position and degree of hydroxylation of the ring structure. All flavonoids with the 3`, 4`-dihydroxy(ortho-dihydroxy) posses marked antioxidant activity. And antioxidant activity increases with the number of hydroxyl groups substituted on the A-and B-rings. There is as yet no certainty about the effect of the presence of a double bond between C\ulcorner and C\ulcorner on the antioxidant activity of flavonoids.

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Pharmacological Activities of Flavonoids (III) Structure-Activity Relationships of Flavonoids in Immunosuppression

  • Kim, Chang-Johng;Cho, Seung-Kil
    • Archives of Pharmacal Research
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    • v.14 no.2
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    • pp.147-159
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    • 1991
  • Effects of twenty-one different flavonoids and their related compounds on the phagocytosis of colloidal carbon by macrophages in liver and spleen humoral immune responses against bacterial $\alpha$-amylase and cellular immune responses against oxazolone and dinitrofluorobenzene were studied in vivo and in vitro. It was shown that most of the flavonoids accelerated significantly the phagocytosis, and they suppressed significantly not only humoral and cellular immune responses but also the development of immunological memory after the antigenic stimulation. Especially, malvin was the most active in phagocysis, and disodium cromoglycate and morin were the most active in humoral and cellular immunosuppression, respectively. Daidzuin had the most potent inhibitory activity in the development of memory cells. The structure-activity relationships of the flavonoids in immunosuppression became apparant from these results: 1. The presence of $C_{2-3}$ double bond and $C_4$ Ketone group in C-ring was important for their immunosuppressive activity. 2. Flavonoids with benzene ring at 2 or 3 position in C-ring showed the almost same activities. 3. The opening of C-ring did not affect their immunosuppressive activity. 4. The glycosylated flavonoids at 3 position in C-ring were less less potent than their aglycones. 5. Di-or tri-hydroxylated flavonoids in B-ring were more potent than mono-hydroxylated. 6. Chromanochromanone also had the immunosuppressive activity.

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Total Phenolic Compounds and Flavonoids in the Parts of Artichoke (Cynara scolymus L.) in Viet Nam

  • Thi, Bui Ha Thu;Park, Moon-Ki
    • Journal of Environmental Science International
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    • v.17 no.1
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    • pp.19-27
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    • 2008
  • Artichoke extracts are widely used alone or in association with other herbs for embittering alcoholic and soft drinks and to prepare herbal teas or herbal medicinal products in Viet Nam. The objective of this paper was a screening of flavonoids and total phenolic compounds content in the parts of artichoke (Cynara scolymus L.) as flowers, leaves, roots, trunks, stumps, The total phenolic compounds and flavonoids in the parts of artichoke were extracted among 3 extraction methods as methanol extraction (EM1), mixing methanol and water method (EM2) and water extraction method (EM3). Total phenolic compounds and flavonoids were determined by UV/VIS, HPLC techniques. The apigenin 7-O-glucosides, cynarin, narirutin, gallic acid, caffeic acid were found as the main flavonoids constituents in all parts of artichoke. It showed that value of total phenolic compounds and flavonoids by EM3 were higher than that of total phenolic compounds and flavonoids by EM1 and EM2. Furthermore, the results of this study revealed that total phenolic compounds and flavonoids, obtained by these convenient extraction methods, may show the quick efficacy of artichoke in all respects of their quality and quantity.

Analysis of flavonoids in the mature fruit of Vaccinium uliginosum L. of China

  • Hua, Lian Li;Yoshitama, Kunijiro
    • Oriental Pharmacy and Experimental Medicine
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    • v.6 no.1
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    • pp.65-67
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    • 2006
  • In this study, a new extraction method was developed and two kinds of flavonoids were extracted from the mature fruit of Vaccinium uliginosum L. of China. These two kinds of flavonoids were analyzed by spectral and identified by high-performance liquid chromatography (HPLC) and UV/Vis. The extract of the fruit was total acid hydrolyzed. TLC chromatography was subsequently employed to identify the hydrolysate. Two kinds of aglycone flavonoids, quercetin and myricetin, were identified. At the same time PC chromatography was used to identify the monomer sugar in the flavonoids and it was verified as glucose. HPLC, UV/Vis, and Mass spectrum analyses revealed that the flavonoids were quercetin 3-monoglucosides and myricetin 3-monoglucosides.

Characteristic Features of Cytotoxic Activity of Flavonoids on Human Cervical Cancer Cells

  • Sak, Katrin
    • Asian Pacific Journal of Cancer Prevention
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    • v.15 no.19
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    • pp.8007-8018
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    • 2014
  • Cervical cancer is the most common gynecologic malignancy worldwide and development of new therapeutic strategies and anticancer agents is an urgent priority. Plants have remained an important source in the search for novel cytotoxic compounds and several polyphenolic flavonoids possess antitumor properties. In this review article, data about potential anticarcinogenic activity of common natural flavonoids on various human cervical cancer cell lines are compiled and analyzed showing perspectives for the use of these secondary metabolites in the treatment of cervical carcinoma as well as in the development of novel chemotherapeutic drugs. Such anticancer effects of flavonoids seem to differentially depend on the cellular type and origin of cervical carcinoma creating possibilities for specific targeting in the future. Besides the cytotoxic activity per se, several flavonoids can also contribute to the increase in efficacy of conventional therapies rendering tumor cells more sensitive to standard chemotherapeutics and irradiation. Although the current knowledge is still rather scarce and further studies are certainly needed, it is clear that natural flavonoids may have a great potential to benefit cervical cancer patients.

Quantitative Distribution and Analysis of Methoxylated Flavonoids in Citruses and Korean Chung-pi (감귤류와 한국산 청피에 함유된 Methoxylated Flavonoids의 분석과 정량적 분포)

  • Baik, S.O.;Bock, J.Y.;Chun, H.J.;Jeong, S.I.;Han, W.S.;Kim, I.K.
    • Analytical Science and Technology
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    • v.14 no.4
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    • pp.331-339
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    • 2001
  • Methoxylated flavonoids (sinenstin, nobiletin, tangeretin) were isolated and identified by preparative HPLC, mass and NMR. Chung-pi(I) and Chung-pi(II) contained methoxylated flavonoids most richly. Methoxylated flavonoids in Chung-pi obtained from Korean Milgam increased with fruit maturity, while contents of the methoxylated flavonoids gradually decreased after mid of October.

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Free Radical Scavenging of Flavonoids and Their Effects on Erythrocyte Na Leak, Platelet Aggregation and TBARS Production

  • Lee, Ji-Hyun;Kang, Young-Hee;Kang, Jung-Sook
    • Nutritional Sciences
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    • v.5 no.4
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    • pp.197-202
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    • 2002
  • We compared the radical scavenging activity of flavonoids and their antioxidant effects on erythrocyte Na leak, platelet aggregation and TBARS (thiobarbituric acid reactive substance) production, using Sprague Dawley rats. The concentrations of flavonoids needed for scavenging radicals by 50% ($SC_{50}$) in 0.1mM DPPH (2,2 Diphenyl 1-picryl hydrazyl) were: Quercetin, 7.4/$\mu$M; Catechin, 10.6$\mu$M; Morin, 22$\mu$M; Hesperidin, 400uM; and Naringin, 3.95mM. Morin completed its antioxidant activity in 2 minutes, while catechin, hesperidin and naringin had slow but long lasting antioxidant activity. Whole blood platelet aggregation, when incubated with quercetin or catechin, was significantly decreased (P<0.05) compared with the control. Sodium leak in intact erythrocytes was significantly lower when incubated with quercetin, compared with other flavonoids (P<0.05). Morin, hesperidin and naringin somewhat increased Na leak in intact erythrocytes. Sodium leak in erythrocytes treated with phenazine methosulfate (PMS) was increased overall, but was not affected by flavonoids. Intracelluar Na and K were not affected by treatment with PMS. TBARS production in platelet rich plasma (PRP) was significantly lower (P<0.05) than the control when incubated with quercetin or hesperidin. PMS treatment caused an increase in TBARS production regardless of flavonoids. In the present study antioxidant effects of flavonoids were not well correlated with their radical scavenging activities, although quercetin, which showed the strongest radical scavenging activity, had the greatest antioxidant effect.

Inhibitory Aromatase Effects of Flavonoids from Ginkgo Biloba Extracts on Estrogen Biosynthesis

  • Park, Yong Joo;Choo, Wun Hak;Kim, Ha Ryong;Chung, Kyu Hyuck;Oh, Seung Min
    • Asian Pacific Journal of Cancer Prevention
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    • v.16 no.15
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    • pp.6317-6325
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    • 2015
  • Ginkgo biloba extract (GBE) is a popular phytomedicine and has been used for disorders of the central nervous system, cardiovascular, renal, respiratory, and circulatory diseases. Although GBE is a complex mixture of over 300 compounds, its major components are 24% flavonoids and 6% terpene lactones. In this study, we tested the inhibitory effects of the three major flavonoids (kaempferol, quercetin, and isorhamnetin) from GBE, independently and as mixtures, on aromatase activity using JEG-3 cells (human placental cells) and recombinant proteins (human placental microsome). In both systems, kaempferol showed the strongest inhibitory effects among the three flavonoids; the flavanoid mixtures exerted increased inhibitory effects. The results of exon I.1-driven luciferase reporter gene assays supported the increased inhibitory effects of flavonoid mixtures, accompanied by suppression of estrogen biosynthesis. In the RT-PCR analysis, decreased patterns of aromatase promoter I.1 mRNA expressions were observed, which were similar to the aromatase inhibition patterns of flavonoids and their mixtures. The present study demonstrated that three flavonoids synergistically inhibit estrogen biosynthesis through aromatase inhibition, decrease CYP19 mRNA, and induce transcriptional suppression. Our results support the usefulness of flavonoids in adjuvant therapy for breast cancer by reducing estrogen levels with reduced adverse effects due to estrogen depletion.

Modulation of Activator Protein-1 (AP-1) and MAPK Pathway by Flavonoids in Human Prostate Cancer PC3 Cells

  • Gopalakrishnan, Avanthika;Xu, Chang-Jiang;Nair, Sujit S.;Chen, Chi;Hebbar, Vidya;Kong, Ah-Ng Tony
    • Archives of Pharmacal Research
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    • v.29 no.8
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    • pp.633-644
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    • 2006
  • In last couple of decades the use of natural compounds like flavonoids as chemopreventive agents has gained much attention. Our current study focuses on identifying chemopreventive flavonoids and their mechanism of action on human prostate cancer cells. Human prostate cancer cells (PC3), stably transfected with activator protein 1 (AP-1) luciferase reporter gene were treated with four main classes of flavonoids namely flavonols, flavones, flavonones, and isoflavones. The maximum AP-1 luciferase induction of about 3 fold over control was observed with $20\;{\mu}M$ concentrations of quercetin, chrysin and genistein and $50\;{\mu}M$ concentration of kaempferol. At higher concentrations, most of the flavonoids demonstrated inhibition of AP-1 activity. The MTS assay for cell viability at 24 h showed that even at a very high concentration $(500\;{\mu}M)$, cell death was minimal for most of the flavonoids. To determine the role of MAPK pathway in the induction of AP-1 by flavonoids, Western blot of phospho MAPK proteins was performed. Four out of the eight flavonoids namely kaempferol, apigenin, genistein and naringenin were used for the Western Blot analysis. Induction of phospho-JNK and phospho-ERK activity was observed after two hour incubation of PC3-AP1 cells with flavonoids. However no induction of phospho-p38 activity was observed. Furthermore, pretreating the cells with specific inhibitors of JNK reduced the AP-1 luciferase activity that was induced by genistein while pretreatment with MEK inhibitor reduced the AP-1 luciferase activity induced by kaempferol. The pharmacological inhibitors did not affect the AP-1 luciferase activity induced by apigenin and naringenin. These results suggest the possible involvement of JNK pathway in genistein induced AP-1 activity while the ERK pathway seems to play an important role in kaempferol induced AP-1 activity.